Carbon Dioxide → HCID 14621981, compound

HRID 1534782Notes

Reaction equation

HRID 1534782 reaction equation
C([Li])CCC.Br[CH:7](Br)[CH2:8][C:9]1[C:10]([CH:28]([CH3:30])[CH3:29])=[N:11][C:12]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:13][C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1.[C:32](=[O:34])=[O:33].Cl>CCCCCC.C1COCC1>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:14]2[CH:13]=[C:12]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:11]=[C:10]([CH:28]([CH3:29])[CH3:30])[C:9]=2[C:8]#[C:7][C:32]([OH:34])=[O:33])=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 19908295HCID 19908295, compoundHCID 178418339Butyllithium

Product 1

HCID 14621981HCID 14621981, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

30.3 ml (48.4 mmol) of a 1.6M solution of n-butyllithium in hexane were added dropwise at -70° C. to a solution of 11.5 g (24.2 mmol) of 1,1-dibromo-2-(4-(4-fluorophenyl)-2-(1-methylethyl)-6-phenylpyridin-3-yl)ethane (Example 1a) in 70 ml of THF. The resulting solution was stirred at -70° C. for 1 h and then at room temperature for 1 h and subsequently cooled to -60° C. 10.7 g (242 mmol) of crushed dry ice were added and then the reaction mixture was slowly brought to room temperature, hydrolyzed on ice-water, acidified with dilute hydrochloric acid and extracted several times with ether. The combined organic phases were washed with saturated NaCl solution, dried over MgSO4 and evaporated. The residue was 11.0 g of the title compound which was reacted further without purification. For analytical purposes, a small amount of the crude product was purified on silica gel (dichloromethane/methanol 9:1).

Workup

  1. waitat room temperature for 1 h
  2. temperaturesubsequently cooled to -60° C
  3. customwas slowly brought to room temperature, hydrolyzed on ice-water
  4. extractionextracted several times with ether
  5. washThe combined organic phases were washed with saturated NaCl solution
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customwas reacted further without purification
  9. customFor analytical purposes, a small amount of the crude product was purified on silica gel (dichloromethane/methanol 9:1)

Sources & evidence

ORD record
ord-dcd7c10072a24663816e10d4a46cd87e
Source dataset
uspto-grants-1992_02
Patent number
US05091386

Reaction notes

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